Organic electroluminescent materials and devices

Abstract

A compound of Formula I:wherein each R1, R2, R3, and R4 is independently hydrogen or a substituent selected from the group consisting of deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, carbonyl, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, boryl, and combinations thereof; andwherein any two adjacent substituents are optionally joined or fused together to form a ring.

We claim: 
     
       1. An organic light emitting device (OLED) comprising:
 an anode; 
 a cathode; and 
 an organic layer, disposed between the anode and the cathode, comprising a first compound of Formula I: 
 
       
         
           
           
               
               
           
         
         wherein each R 1  and R 2 , is independently hydrogen or a substituent selected from the group consisting of deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, carbonyl, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, boryl, and combinations thereof; 
         wherein any two adjacent substituents are optionally joined or fused together to form a ring; 
         wherein each R 3  and R 4  is independently a substituent selected from the group consisting of alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, sulfanyl, sulfinyl, sulfonyl, phosphino, boryl, and combinations thereof; and 
         wherein R 3  and R 4  are joined together to form a ring, which is optionally further substituted. 
       
     
     
       2. The OLED of  claim 1 , wherein each R 1  and R 2  is independently hydrogen or a substituent selected from the group consisting of deuterium, halide, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, boryl, and combinations thereof. 
     
     
       3. The OLED of  claim 1 , wherein R 3  and R 4  are joined together to form a 5-membered or 6-membered aromatic ring, which is optionally further substituted. 
     
     
       4. The OLED of  claim 1 , wherein the organic layer is an emissive layer and the first compound is a host. 
     
     
       5. The OLED of  claim 1 , wherein at least one of R 1 , R 2 , R 3 , and R 4  comprises a chemical group selected from the group consisting of: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
       and combinations thereof, or any aza variant thereof. 
     
     
       6. The OLED of  claim 1 , wherein the organic layer further comprises a phosphorescent emissive dopant; wherein the emissive dopant is a transition metal complex having at least one ligand or part of the ligand if the ligand is more than bidentate selected from the group consisting of: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         wherein each Y 1  to Y 13  is independently selected from the group consisting of carbon and nitrogen; 
         wherein Y′ is selected from the group consisting of B R e , N R e , P R e , O, S, Se, C═O, S═O, SO 2 , CR e R f , SiR e R f , and GeR e R f ; 
         wherein R e  and R f  are optionally fused or joined to form a ring; 
         wherein each R a , R b , R c , and R d  independently represents from mono substitution to the maximum possible number of substitution, or no substitution; 
         wherein each R a , R b , R c , R d , R e  and R f  is independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; and 
         wherein any two adjacent substituents of R a , R b , R c , and R d  are optionally fused or joined to form a ring or form a multidentate ligand. 
       
     
     
       7. The OLED of  claim 1 , wherein the organic layer is a blocking layer and the first compound is a blocking material in the organic layer. 
     
     
       8. A consumer product comprising an organic light-emitting device (OLED) comprising:
 an anode; 
 a cathode; and 
 an organic layer, disposed between the anode and the cathode, comprising a first compound of Formula I: 
 
       
         
           
           
               
               
           
         
         wherein each R 1  and R 2 , is independently hydrogen or a substituent selected from the group consisting of deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, carbonyl, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, boryl, and combinations thereof; 
         wherein any two adjacent substituents are optionally joined or fused together to form a ring; 
         wherein each R 3  and R 4  is independently a substituent selected from the group consisting of alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, sulfanyl, sulfinyl, sulfonyl, phosphino, boryl, and combinations thereof; and 
         wherein R 3  and R 4  are joined together to form a ring, which is optionally further substituted. 
       
     
     
       9. The consumer product of  claim 8 , wherein the consumer product is selected from the group consisting of a flat panel display, a computer monitor, a medical monitor, a television, a billboard, a light for interior or exterior illumination and/or signaling, a heads-up display, a fully or partially transparent display, a flexible display, a laser printer, a telephone, a cell phone, tablet, a phablet, a personal digital assistant (PDA), a wearable device, a laptop computer, a digital camera, a camcorder, a viewfinder, a micro-display that is less than 2 inches diagonal, a 3-D display, a virtual reality or augmented reality display, a vehicle, a video walls comprising multiple displays tiled together, a theater or stadium screen, a light therapy device, and a sign. 
     
     
       10. A compound of Formula I: 
       
         
           
           
               
               
           
         
         wherein R 1  and R 2 , are each are each independently selected from the group consisting of deuterium, halide, alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, nitrile, isonitrile, sulfanyl, boryl, and combinations thereof; 
         wherein any two adjacent substituents are optionally joined or fused together to form a ring; 
         wherein R 3  and R 4  are each independently selected from the group consisting of alkyl, cycloalkyl, heteroalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, aryl, heteroaryl, sulfanyl, boryl, and combinations thereof; 
         wherein R 3  and R 4  are joined together to form a ring, which is optionaly further substituted; and 
         wherein at least one of R 1 , R 2 , R 3 , and R 4  comprises a chemical group selected from the group consisting of: 
       
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
       and combinations thereof, or any aza variant thereof. 
     
     
       11. The compound of  claim 10 , wherein R 3  and R 4  are joined together to form a fused 5-membered or 6-membered aromatic ring, which is optionally further substituted. 
     
     
       12. The compound of  claim 10 , wherein the compound is selected from the group consisting of Formulas I-X: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         wherein Z is O, NR 5  or S; 
         wherein at least one of R 1 , R 2 , and R 5  is independently selected from the group consisting of: 
       
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         wherein the remaining R 1  and R 2 , in Formula I are independently hydrogen, phenyl, biphenyl, naphthalene, or pyridine; and 
         wherein the remaining R 1 , R 2 , and R 5  in Formulas II-X are independently hydrogen, phenyl, biphenyl, naphthalene, or pyridine. 
       
     
     
       13. A formulation comprising a compound according to  claim 10 . 
     
     
       14. A chemical structure selected from the group consisting of a monomer, a polymer, a macromolecule, and a supramolecule, wherein the chemical structure comprises a compound according to  claim 10 . 
     
     
       15. The OLED of  claim 1 , wherein the organic layer is an emissive layer and the first compound of Formula I is an emissive dopant or a non-emissive dopant. 
     
     
       16. The OLED of  claim 1 , wherein the first compound is an acceptor, and the OLED further comprises a sensitizer selected from the group consisting of a delayed fluorescence emitter, a phosphorescent emitter, and combination thereof. 
     
     
       17. The OLED of  claim 1 , wherein the first compound is a fluorescent emitter, a delayed fluorescence emitter, or a component of an exciplex that is a fluorescent emitter or a delayed fluorescence emitter. 
     
     
       18. The OLED of  claim 1 , wherein the first compound is a sensitizer, and the OLED further comprises an acceptor selected from the group consisting of a fluorescent emitter, a delayed fluorescence emitter, and combination thereof.